Thiophene synthesis - Organic Chemistry Portal
Benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones were synthesized by Abdel-Aziz and Mekawey and evaluated for antifungal and antibacterial activities. The antifungal potencies were superior to the antibacterial activities in these series. Compound 22 was found to be a promising antifungal agent. From the results of the morphological features of A. fumigatus and C. albicans, it can be concluded that these derivatives can be considered very promising in the perspective of new drugs discovery.
Indole chemistry began to develop with the study of the dye indigo
Kenchappa et al. synthesized a novel series of benzofuran derivatives, containing barbitone and thiobarbitone moiety. The investigation of antimicrobial screening of this compounds revealed that all compounds exhibited a varied degree (MIC, 11.38-199.10 mmol/L) of antibacterial activity against all tested bacterial strains. SAR studies revealed that electron withdrawing groups in the ortho position of benzofuran ring and in the para position of aryl ring have a tendency to increase the potency while compounds containing electron-donating groups were found to weaken the antimicrobial activity. Compounds 23 and 24 having two bromo substituents on C-5 of benzofuran and C-4 of phenyl ring, respectively, were found to exhibit excellent antibacterial activity against all tested bacterial strains with MIC value of 29.76-31.96 mmol/L. Compounds bearing -Br substituent on C-4 position of the aryl ring showed good ability to inhibit S. tyhphi at MIC 36.61-37.92 mmol/L; the same compounds showed good activity against P. syringae with MIC 37.20-38.50 mmol/L while compounds having hydroxyl and bromo substituent exhibited moderate to good activity against S. tyhphi with MIC value 36.08-36.73 mmol/L. The MIC of antifungal activity of the compounds indicated that compounds 25 and 26 exhibited remarkable activity against the tested organisms with MIC value 14.90-29.92 mmol/L. Further, the synthesized compounds were studied for docking on the enzyme, glucosamine-6-phosphate synthase, and the results showed that compounds 23 and 24 emerged as an active antimicrobial agents with lowest binding energy (−5.27 kJ mol/L and −4.85 kJ mol/L, respectively).
Fused benzofuran derivatives containing coumarin and pyridine rings (30) were synthesized by Khan et al. and their antibacterial and antifungal activities were evaluated. In antibacterial screening, all compounds showed MIC of 25 μg/mL against P. chinchori but they were ineffective against M. aureus. In antifungal screening, the compounds showed MIC at 25 μg/mL and 100 μg/mL against A. fumigatus and P. wortmanni, respectively.
JMCS - Journal of the Mexican Chemical Society
Objective: Synthesis of novel 2-(1-benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinoline-4-carbohydrazide and its derivatives for antimicrobial and antitubercular activity.
The Journal of the Mexican Chemical Society (J
General procedure for the synthesis of (1-benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinoline-4-carbo-hydrazide and its derivatives 2(a-b), 3(a-b), 4(a-b), 5(a-b) and 6(a-b)
methoxymethyl pyrazine 63450-30-6
Manna and Agrawal demonstrated that some indophenazine 1,3,5-trisubstituted pyrazoline derivatives of benzofuran (9), which were synthesized by microwave irradiation, exhibited good antibacterial activity with MICs lower than 10 μg/mL against E. coli, P. aeruginosa and S. aureus, which was comparable with sparfloxacin and norfloxacin.
General & Introductory Chemistry
Scheme 1: Synthesis of 2-(1-benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinoline-4-carbohydrazide and its derivatives 2(a-b), 3(a-b), 4(a-b), 5(a-b) and 6(a-b)
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A simple and effective approach was described for the synthesis of (1 benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinolone-4 carbohydrazide and its derivatives 2(a-b), 3(a-b), 4(a-b), 5(a-b) and 6(a-b) in good yield. Analogues were made to predict ADMET/SAR in silico, the synthesized molecules are in the acceptable range were further screened for antimicrobial and antitubercular activity. The present work indicates that synthesized molecules were found to possess good antitubercular and potent antimicrobial activity. The above results indicate that the core moiety benzofuran, quinoline and isatin are essential for antimicrobial and antitubercular activity. The fluoro substitution at 8th position of the quinoline ring and nitro, bromo, fluoro substituted on isatin ring is essential for the activity. The results provide useful information for operating as a positive reinforcement of the tendency to use antimicrobial and antitubercular properties as a guideline of the rational design of this class of compounds.